Date: Sat, 12 May 2001 10:18:14 -0400
From: Joyce Devries
Subject: Fantasy Date
SECRET DATE
My First Real Date,
By Joyce Devries, joyce_devries@hotmail.com
October 1986
Note, this a true story, some of the names have been changed, but
certainly not the events of the days!, this is taken right from my
diary entry of the time.
My (email) name is Joyce Devries and it was a real life adventure
I will never forget, my first time I pleased a male as a woman with my
mouth. I am 5'2", TV, live near Toronto, Ont., Canada, pass quite well
as a woman and have done tons of "real life" things as a woman, but
this was my first.
I am about to let you know of something that happened to me
approximately 16 years ago, that to this date, my girlfriend at the
time, now my wife will never find out about. It is for that reason
that the following true story will not use real names, nor places, but
all the details are true. I am a TV and a heterosexual one at that,
but this incident, something for a brief period, changed my whole look
on myself, and how I now treat women, and that is with a great deal of
respect and admiration.
I was 20 at the time and was living in an apartment all by
myself, I had no current girlfriend and since moving out two years
prior to this date, I was totally engulfing myself into dressing and
behaving like a normal female. I started dressing very early in life
and like to call myself Joyce, I always thought I looked like one. I
was about the same height I am now, 5'2", and still have the same long
brown haired wig. I have about a 36B chest and loved to wear tight
sweaters to show it off. I spent most of my time alone with a camera
and videotaped myself over and over, I practiced walking, talking,
sitting, eating, sitting, the whole thing. I would often go to malls
as a male and just sit and watch females as they went about their
normal activities, I would take mental notes and immediately go home
and practice what I had seen.
For about a year after I moved away from home, I never appeared
in public, but I always thought I could, as my look, walk, talk and
dressing style was good. I would always go shopping for my 'sister'
and 'girlfriend' and knew exactly what size to get, at that time I was
a 12 dress, and 7 shoe, I found those out by accident. I had built up
quite the collection, and always was fashion aware and bought many
items that coordinated together and accessories that blended in well.
Then one day I got the nerve to finally go out. It was a Saturday and
the malls were full of Christmas shoppers and I was sure I could blend
into the crowds.
I started by getting ready with a ritual I had become an expert
in, I shave as close as possible my entire body, so that my skin was
as soft as a baby. Next I pampered myself with a long, relaxing bath
in scented bubbles, then powdered myself with a sweet scented powder.
I then donned my wig, brushing and styling it to perfection, moving to
my room and makeup table from the washroom, I applied makeup, bronze
and light gold to my eyes, brown mascara, brown eyeliner, soft pink
blush and a satin pink lipstick. Choosing my clothes for the day was
rather tough as I wanted to appear so perfect yet, not too dressy. I
chose standard undergarments, bra, slip, camisole, panties and nude
colored nylons, I wore a loose, Flouncy jean skirt, and a light blue
turtleneck and low, 2 inch heels. I grabbed my purse and slipped into
my coat and walk down to a local mall.
Once in the mall, no attention was even paid to me, I expected to
be looked up and down by everyone, but nobody even stared me down, oh
except for a few guys and they gave me looks, but they were admiring,
not laughing. I slowly lost my nervousness and sort of got a great
'high' as I walked around. I then decided to be like so many females I
have watched in my 'staring' sessions and take a stroll into a popular
ladies store, and lone behold I got the thrill of my life. While
browsing through a rack of skirts, a salesgirl walked up to me and
asked if I needed any help, well I was on such a high, I spoke in my
practiced feminine voice and said, not really just browsing, she
smiled and said, "just ask for me if you need any help, my name is
Anne", and I said thank you and continued browsing. I spent the whole
day in the mall, walking from store to store, looking at everything
feminine, lingerie, dresses, skirts, stockings, I never thought it
could be this good. I left the mall a changed 'woman' and went home to
bask in my joy, and vowed that next trip would be to a bar on ladies
night, and that I wanted to really see if I could prove to myself I
was that convincing of a woman.
The big day arrived, I got off work early and came home to shave
and dress, it was a Thursday night and I had Friday off. I wanted to
be careful how I dressed and how I did my makeup, so I decided on a
pretty black velvet skirt and a sheer feminine white blouse with the
appropriate camisole underneath. My makeup was done almost the same as
shopping, but because of the low light, I used black eyeliner and
mascara and did my blush a little lighter, I also let my nails grow
for the occasion and colored them the same shade as my lipstick. Along
with the skirt and blouse I decided on wearing my black patent 3 inch
heels and added a modest spritz of Obsession perfume.
It was 7pm and I left for the bar, it was in the same mall I was in
the previous week. I sauntered around to the door and was greeted by a
gentleman who addressed me, "welcome madam, hope you have a good
time", and was escorted to a table by the waitress. I ordered only a
salad and some drinks and sat by myself as the bar started to fill
with very attractive girls and guys. Then it suddenly donned on me, I
needed to go to the washroom, and that is one thing I was not really
prepared to do. I was not going to spend the whole night in pain, nor
was I going to leave the bar, so I grabbed my purse and headed for the
washrooms.
As I passed the men's washroom, a chill ran down my spine as I could
now hear my heels echoing down the hallway. I gathered my courage and
swung open the door and to my surprise there was nobody in the
washroom, and that was lucky as it was so small, only three stalls, a
sink, and large mirror. I entered a stall and sat down to do my
business, when the door swung open and in walked two other girls, I
was in shock and didn't know what to do, I quickly did my business and
pulled up my nylons and adjusted the front of my skirt. I then left
the stall and noticed my lipstick was smudged, and thought it be
better to adjust it in here rather than at my table, so just as I took
out the tube and started to apply it. Then out walked one of the girls
that came in earlier, I was petrified, but was relaxed when she smiled
and said high and started to do the same as me. I left before the
other came out of her stall, and as I walked back to my table I
thought 'this is great, nothing can stop me now', that's what I
thought.
By the time I sat back down, the time was 9pm, and most people
had stopped eating and started drinking, including myself. I then
thought it appropriate to stroll up to the bar and sit on a stool and
listen to the music, my plan now was simple, to watch other people
dancing and sipping on a few drinks before heading home, when suddenly
I met Rick.
I was approached by a man, about 5'6", with black hair and a mustache,
he was alright looking and I was a little nervous as he sat down next
to me and started some small talk. After about two minutes I knew he
was comfortable with me and I decided to enjoy the conversation. He
asked my name, profession, which I made up, my likes dislikes and so
on. I was so thrilled as now I was seeing what it was like on the
other side of the coin. Rick then made the offer to dance and I
accepted, I had never danced much with girls, much less with a guy
while I was wearing heels, but the song was fast and everything worked
out well. I even followed the lead of other girls on the dance floor,
and placed my purse close by on the floor.
The rest of the evening was spent talking about likes and dislikes and
I found myself making a whole new life for Joyce totally separate from
my male side. Before I knew it the last call was being hailed and Rick
like the perfect gentleman offered me a ride home, and like the
perfect woman, accepted. The ride home was interesting, because I
could see my male self in Rick's eyes, I knew he wanted to ask me out
and I was hoping he wouldn't, but I had the line that I was seeing
someone else all ready. Rick stopped in front of my apartment and I
thanked him for the ride, he said it was no problem at all and felt
quite secure as he made no moves towards me as we were departing. Then
it came out, Rick said, "look Joyce, I've only known you a few hours,
but would like to know you much better. My company is having their
Christmas party this Saturday night, care to go?, I sure would like to
escort you on my arm". I was shocked, a date?, mmmm I thought, what an
opportunity, I had always loved to watch as girls at formal occasions
really turned me on, so I accepted and he agreed to pick me up out
front of the apartment at 6:30 the next night.
At first the idea was thrilling, dressed to the nines and being
treated as the perfect lady, then it donned on me, what shall I wear?,
my wardrobe was mainly casual and semi-formal, and this was sure to be
a very formal occasion, so I decided, Friday would be a shopping day
and I would find my perfect dress, as Joyce, not my male self. When I
went to bed, it was as usual all dressed in lace and satin in a sexy
teddy. As I lay there I thought of what lie ahead and dreamed as I
slowly relieved myself through the satin material, and that as when
the first thoughts of actually what might happen if things got carried
away might do. Mind you they were not entirely disgusting thoughts in
the frame of mind I was in.
As the day begun, I started to get ready, I decided to go for the
'just from the office' look and found a conservative yet pretty
blouse, it was cream colored with a lace colour and decided on a
straight 'A' line black skirt. I wore black pantyhose, some jewelry
and my patent black shoes that I wore the other night, with the 2 inch
heel. I took my time and did my makeup very soft and highlighted all
my best features, I was also very light on the perfume. Colours I used
were my usual for dressing for 'work' and they were soft pink on the
upper lids and light blue on the lower lids, brown mascara, and brown
eyeliner. I did my blush very soft and used my favorite light pink
colored lipstick. I grabbed my coat and purse when I was ready and
headed out the door.
Once inside the mall, I was not even nervous, mind you it as not as
crowded as Saturday, but still, I felt at home and relaxed, I even got
a few approving smiles from other women, who were out from work. I
made my way to the cash machine and withdrew, $150, I thought that
would me more than enough for my dress, I was about to realize how
wrong I was. I had a good idea on what to buy, it had to compliment my
obvious small hips, even with the padding, and have a high collar. I
flipped through a few fashion magazines at home before I left and was
sure I knew what I wanted.
The first store I entered I was immediately aware that the prices were
going to be high, I was greeted immediately by a salesgirl and found
the look inside to be very elegant. I was greeted then asked what I
was after, I explained that I had a Christmas party to attend and that
I was looking for a gown that had a high collar, but one thing I
forgot, colour!, one thing I have found to be so important to females.
I then decided on basic colours and nothing too flashy. I was then
asked what I intended to spend and the salesgirl smiled and politely
said that I would not find anything like that in that particular
store, but she was helpful and offer a couple of stores as solutions.
I then thanked her and headed off to one store she had suggested.
Upon entering that first store, I could tell I would probably
find what I wanted, I had a feeling. Now used to the salesgirls, I
smiled back as a well dressed girl in her early twenties came up to me
and ask if she could be of any assistance and readily agreed. She was
beautiful and wore a short blue shirt dress with heels almost the same
height as mine. I explained to her all the details and she immediately
lead me to a rack of dresses and started pulling out different shapes
and styles. I was having a great time and was in even more awe as she
pulled out a black velvet dress with a satin bow around the waist. She
could instantly tell I was interested and said, "come on, let's see
how this looks on you". The dress had a peplum style skirt, which
ingeniously hides your hips and a high collar, as not to expose your
breasts.
As I entered the change area, I was thrilled and very excited and I
started to undress as the salesgirl carried on small talk. Then the
next problem, I did not really have many dresses with zippers and was
having problems with the zipper. She asked if everything was OK, I
said the zipper was a bit of a problem and she asked if she could
help, I accepted of course and as I appeared from the dressing room
she asked me to turn around and proceeded to do up the zipper. The
dress felt great and the salesgirl was complimenting me and said how
it really pampered my figure. As I stared at myself in the mirror, I
could see she was right, the padded shoulders were making my waist
appear small and it seemed that I had a sexy figure. I was thrilled
and decided right there and then to buy the dress. The salesgirl kept
showering me with compliments and helped me by undoing the zipper at
the back. As I dressed the salesgirl kept on talking to me and
wondered what heels I was going to wear with the outfit, heels?, what
was wrong with the ones I had?, I then decided to ask her what she
thought best, and she suggested that a pretty 4 inch pair would
compliment my stature and make my legs better looking. I thanked her
and after shelling out $125 for the dress left the store and headed
for a shoe store. I found several in the mall but really wanted one
with a female attendant to serve me, and I found one with a pretty
blonde girl in the store.
I entered the store and glanced at the prices and was somewhat
impressed. I expected higher prices. I was greeted by a young lady who
introduced herself as Michelle and offered to be of assistance. I
explained that I was shopping for shoes that matched an outfit I had
just bought, and Michelle then suggested that she see the outfit to
get a better idea as to what would be best. After looking at the
outfit, Michelle suggested the same as the girl in the dress shop, a 4
inch pair of patent black heels and proceeded to measure my foot. I
cannot tell you how excited I was as Michelle fondled my stockinged
feet in the measuring device, I was afraid my gaff on would not hold
as I could see right down her blouse and could see a lacy bra covering
two lovely breasts. "There, you are an 7 with medium width, I'll be
right back", said Michelle as she finished her measurement.
About one minute later she returned and removes two beautiful, yet
high heels and proceeds to have me slip into them. They felt fantastic
and as I stood. I am just a tad wobbly and Michelle suggests a few
practice steps are necessary, and as I walk back and forth I can feel
my calf muscles start to bunch up and realize that my walk is much
more sexy. All the time I am walking, Michelle is asking how they feel
and I can only say great. I then sat down and Michelle removed them
from my feet and I said that I would buy them and Michelle smiled and
said, "well if you are going to be wearing these soon, I suggest you
practice, they take a little getting used to OK". I said OK, and
proceeded to slip back into my low heels, and went to the cash and
paid.
I left the store feeling great and on may way out decided to
check out one of the little jewelry store to see if there was in fact
something to match the outfit and there was. I immediately spotted
some fake diamond clip on earrings and matching bracelet, they were
perfect, and the salesgirl complimented me on my purchases and I
headed for home.
I spent the rest of the day dressed and relaxed around the house
dreaming and wondering about what the next night would be like. I
spent Saturday, making sure I was perfect, I must have shaved about
four times just to be sure and watched all my tapes to be sure that I
was going to be the perfect date for Rick. Around 3pm, I decided that
it was time to get ready for the big date and proceeded to take a long
hot scented bath, one that both relaxed me and allowed for my body to
absorb all of the lovely smells.
Once finished in the bath, I dusted my whole body with my body powder,
leaving me smell fresh and feminine. Next I made my way to the bedroom
and proceeded to don my lingerie, first my special and most favorite,
black lacy padded bra. Following that there was a gaff, the matching
panties to the bra, a dark blue full slip and I thought about my
choice of pantyhose versus garters and stockings and decided to go
with the latter, and finally my silk housecoat and next I was ready
for the makeup table.
I applied my makeup darker than usual with dark blue on the lower lids
and a shade above my normal pink, on the upper. I applied my blush
heavier than normal, making sure my cheeks were visible and chose a
bolder colour of pink lipstick for the overall appearance. I was all
finished my makeup application, when it donned on me, how an I going
to do my dress up?, it was easy in the store, I had a hand, but that
didn't stop me, I came up with the idea of tying a string to the
zipper and doing it up and simply cutting the string off when I was
finished, and amazingly enough it worked, although I lost a few hairs
in the process.
I then slipped into my new heels, which for the first while were
killing my feet, but the nervousness calmed that pain. After that I
donned my jewelry, spritzed myself with some obsession perfume (Rick
loved when I wore it the other night), packed my purse with all the
necessary makeup and that was it, I was ready. So there I stood,
staring at myself in my full length mirror and I looked fantastic,
even I would want to date me, then the same thought that haunted me
the night before came to mind, was I too good looking?, what would
Rick really want from me, and more importantly, would I be so aroused
or mystified to go along with anything?, I was scared at that point
but like everything else decided to play it as things came. I then sat
down, relaxed and waited for the time to come, and around 6:25, I
donned my winter coat, and grabbed my purse and headed down to the
front lobby to wait for Rick.
Rick was promptly on time and made a point of coming out of the
car and escorting me to the passenger side, were he opened the door
and made sure I was comfortably seated before closing it. Rick then
scurried around the car and jumped in, he complimented me a few times
in a row at my appearance, I was taken back and think I managed to
blush. Rick was such a gentleman, he presented me with a corsage and I
pulled my coat back and allowed him to pin it to my dress. I was
already in seventh heaven before the date really had begun, I thanked
Rick and then thought, what would a real girl do if she in my shoes. I
very quickly, went up beside Rick's cheek and kissed it lightly, not
sexual or anything, just light and friendly, Rick smiled then put the
car in gear and were off. Rick was wearing a blue sport jacket and
white shirt with a red tie, he also had on Grey pants and good looking
shoes, he wasn't exactly Burt Reynolds but he was ok. On the way we
chatted about different things and just generally discussed the
weather and music I was into etc., Rick also once again, complimented
me on my dress and said that I would really like meeting his friends
and I looked forward to it.
When we arrived at the hall, Rick quickly made his way to my door
and opened it, just like the perfect gentleman, and I slowly slid my
legs across keeping my knees together and accepted his hand as I left
the car. I felt great walking to the front door, I allowed Rick to
escort me by grabbing his arm. As we got closer to the door I could
hear the clicks of other girls heels and felt that much more feminine
as I knew mine were part of the 'choir'. Once in the door, Rick took
my coat and went and checked them in, I was left sitting just outside
the door to our banquet room and got a good look at the other girls
walking in and just about died. They looked fantastic and I fit right
in, I got a few smiles from some and hellos from the men.
When Rick returned he offered his arm and I accepted and away we went.
Rick found his friends and I was really nervous as I approached the
table, but I had come too far to turn back and I smiled as I was
introduced. There were three of his friends there and they all had
dates, I was seated next to one, Carol, as Rick went and got me a
glass of white wine. Carol immediately started talking to me and I was
even more nervous as I had never really talked 'girl' talk with
another girl, but I seemed to make out ok. She asked pretty small-talk
style of questions, including how long have you and Rick been
together?, I managed to answer that one without too much difficulty.
Rick then returned with the drinks and we sat and sipped and talked, I
was having a great time. After awhile Carol grabbed her purse and
said, "care to go to the washroom Joyce?", at first I was thinking?, I
don't have to go?, but then I remembered always seeing girls going to
the washroom in pairs, "tag-team", we called it and then grabbed for
my purse and said, "sure". The trip to washroom was fantastic, the
washroom was big and very well lit, especially the makeup mirror area,
and all the girls in the washroom were all dressed up and some were
definite knockouts. I went to the stall and went the best I could and
when I came out there was Carol at the makeup mirror and I walked up
to the counter and joined her. Both her and I were applying lipstick
and I felt fantastic, we then left and headed back to the table, and
at this point I was getting very aroused.
Once back at the table we sat and chatted, then ate dinner and killed
two bottles of wine, which made me rather lightheaded. The music
started and once that did, Rick asked me to dance and I of course
accepted. The dancing was different than before, this time, it was
either the wine or the clothes, but I truly thought I was a female and
was feeling quite aroused towards my date. The song was slow and it
seemed to go on forever, and Rick hugged me gently then started to
caress my velvet covered backside and I actually enjoyed it, I made no
attempt to stop him and just hugged him even more.
Rick then continued to caress and I was getting quite aroused by his
touch and allowed him to continue, although my own sex had started to
harden and I could feel it pressing quite hard against my panties and
gaff. I did my best to push slightly away from Rick in the crotch area
to avoid being found out. The petting and caressing of my rear was the
first step and as the night and the drinks flowed along, so did Rick's
advances. I made two or three more trips to the washroom and one of
them Carol joined me and at the makeup counter we chatted and she
mentioned that Rick and I make a cute couple and that Rick never
really has had a girlfriend before.
I left the washroom and returned to the table, it was getting near the
end of the night and I was glad because my feet were just killing me.
I was about to suggest that we leave when a really slow song came on
and Rick asked to dance again and I accepted. Within 2 minutes after
we started dancing, Rick had his hands on my rear again, this time I
reciprocated and then about 2 minutes later, looked up at Rick and
stared at him, he was lost in thought, staring at me like I never will
forget. Then I don't know who moved first, but our heads merged
together and he kissed me, gently and romantically, I accepted and
then as if it was natural, lower my hand to the front of his pants and
'accidentally' caressed his now very hard cock. I was lost at this
point, I started reacting to feelings I had never had before, I was
drunk both from the alcohol and from the lust and thrill of being an
attractive female.
After the song Rick suggested we leave and we finished our drinks said
our good byes and headed to the car. Once inside the car we kissed
again, this time harder and longer, then the fateful question, "Joyce,
care to come back to my place for a drink?", and that is were I drew
the line, I would not spoil a whole evening for Rick nor place myself
in an danger, so with my 'new' personality, offered Rick a solution,
and that was to find a quiet place to 'park' and he liked the idea.
He took me to the favorite area make out spot and shut the engine off,
he then suggested we go into the backseat to get more comfortable and
I agreed. Once in the backseat, Rick moved quickly to have me in his
arms and kissed me passionately, I graciously accepted and made a
point of gently caressing his cock, which by now was so wet that I
could feel it through his pants. Rick was enjoying my breasts through
my dress and then suggested we get more 'comfortable' and that is
where I drew the final line. I felt sorry for Rick that I had lead him
on so long and that I never could live up to his date and felt like I
really had cheated him and made a fool of him. I explained that I was
on my period and that if he liked I could relieve him in another way.
I was scared and very nervous at this point and as it turned out Rick
was lost at what I was talking about and then I committed myself to
giving Rick his first and me giving my first blow job. I laid Rick back
and slowly undid his belt and pants, all the time telling Rick to relax
and enjoy. I undid the belt then the pants and pulled them off, and
staring at me was a pair of white underwear and a large rod holding
them out like a tent.
Rick was nervous as I slid the underwear off and lone behold I was
staring a rock hard cock. It was not that big and I proceeded to lick
the head while caressing the balls. This was all very new to me, yet I
had watched enough videos to know the technique. Soon Rick was
enjoying the caressing and was moaning and squirming his hips. I then
took the whole cock in my mouth and began to pump up and down, and all
the while Rick was caressing my hair, I actually felt quite feminine
and started to enjoy the sensation. Then Rick started to tense up and
his cries became louder and louder, I knew he was going to cum and
braced myself for it, he shot a huge load and I swallowed each and
every drop, I was actually quite proud. Once Rick had finished I
licked him clean and came back up to kiss him, he didn't like that
idea too much, but was grateful for the relief. We chatted a little
more about the future and I had always told him that I had a steady
boyfriend who was out off town, and started to give him the idea that
this was the be all and end all of our relationship. Rick then drove
me home and dropped me off, not before a long a lingering goodbye
kiss.
I then went up to my apartment, kicked off my shoes, managed to get
out of my dress then put on my favorite teddy and headed to bed were I
relieved myself onto the silky material and thought about the days and
nights events, and fell into a blissful sleep.
If you liked this true life adventure, let me know, maybe one day it
might be you?
Joyce_devries@hotmail.com